Showing Compound Card for 5-Amino-6-ribitylamino uracil (CDB004992)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:58:09 UTC
Updated at2020-11-18 16:39:10 UTC
CannabisDB IDCDB004992
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5-Amino-6-ribitylamino uracil
Description5-Amino-6-ribitylamino uracil, also known as 5-arpd or 6-(1-D-ribitylamino)-5-aminouracil, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Amino-6-ribitylamino uracil is an intermediate in riboflavin metabolism. 5-Amino-6-ribitylamino uracil is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Amino-6-ribitylamino uracil exists in all living species, ranging from bacteria to humans. It is converted from 5-amino-6-(5'-phosphoribitylamino)uracil via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC3.1.3.-). Outside of the human body, 5-Amino-6-ribitylamino uracil has been detected, but not quantified in, several different foods, such as cowpea, garden onion (var.), allspices, sparkleberries, and black huckleberries. This could make 5-amino-6-ribitylamino uracil a potential biomarker for the consumption of these foods. Riboflavin is yellow or yellow-orange in colour and in addition to being used as a food colouring it is also used to fortify some foods including baby foods, breakfast cereals, pastas, sauces, processed cheese, fruit drinks, vitamin-enriched milk products, some energy drinks, and vitamin supplements. However, gut microflora do have the necessary enzymatic machinery to produce and metabolize this vitamin. Riboflavin (or vitamin B2) is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. Humans do not have all the enzymes needed to synthesize or metabolize riboflavin. It is considered to be the second product of the riboflavin synthase reaction (PMID: 14245407 ). It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. 5-Amino-6-ribitylamino uracil is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Amino-6-(D-ribitylamino)uracilKegg
6-(1-D-Ribitylamino)-5-amino-2,4-dihydroxypyrimidineKegg
6-(1-D-Ribitylamino)-5-aminouracilKegg
4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidineKegg
5-a-RUHMDB
5-Amino-2,6-dioxo-4-ribitylaminopyrimidineHMDB
5-Amino-6-(1-D-ribitylamino)uracilHMDB
5-Amino-6-ribitylamino-2,4-(1H,3H)pyrimidinedioneHMDB
5-Amino-6-ribitylaminouracilHMDB
5-ArpdHMDB
a-4-RAPHMDB
1-[(5-Amino-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinyl)amino]-1-deoxy-D-ribitolHMDB
4-(1'-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidineHMDB
4-(1’-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidineHMDB
4-(Ribitylamino)-5-aminouracilHMDB
4-Ribitylamino-5-amino-2,6-dihydroxypyrimidineHMDB
5-Amino-4-D-ribitylaminouracilHMDB
5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedioneHMDB
ARPHMDB
5-Amino-6-ribitylamino uracilHMDB
Chemical FormulaC9H16N4O6
Average Molecular Weight276.25
Monoisotopic Molecular Weight276.107
IUPAC Name5-amino-6-{[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Name5-arpd
CAS Registry Number17014-74-3
SMILES
NC1=C(NC[C@H](O)[C@H](O)[C@H](O)CO)NC(=O)NC1=O
InChI Identifier
InChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)/t3-,4+,6-/m0/s1
InChI KeyXKQZIXVJVUPORE-RPDRRWSUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Polyol
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area177.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.48 m³·mol⁻¹ChemAxon
Polarizability25.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Amino-6-ribitylamino uracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0903-9440000000-d4b6a6cff43cc761315fSpectrum
Predicted GC-MS5-Amino-6-ribitylamino uracil, TBDMS_4_38, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Amino-6-ribitylamino uracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Amino-6-ribitylamino uracil, "5-Amino-6-ribitylamino uracil,4TBDMS,#38" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1190000000-2514b630f375b2189bfe2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fu-9750000000-779ce19c1a0e6b0c69322015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-2f9fc8d8f57a4b3ca8c62015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-5490000000-40e672b419cf2a89e7232015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-e4e8a4b406ad4dfd459f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-0e769fc743b8cee3b5422015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-04a8c31cda1ce3aa2de82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-0490000000-f4be226ba3308c6193ea2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9700000000-b24f4f1baf9ef6a124b92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-0290000000-dbb8670827f983a8ba0f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052g-2900000000-2170e047feac108734192021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-c7d08326dc254630e1832021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
14 kDa phosphohistidine phosphatasePHPT1Q9NRX4 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
14 kDa phosphohistidine phosphatasePHPT1Q9NRX4 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011106
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030561
KNApSAcK IDNot Available
Chemspider ID167930
KEGG Compound IDC04732
BioCyc IDAMINO-RIBOSYLAMINO-1H-3H-PYR-DIONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound193516
PDB IDNot Available
ChEBI ID15934
References
General References
  1. WACKER H, HARVEY RA, WINESTOCK CH, PLAUT GW: 4-(1'-D-RIBITYLAMINO)-5-AMINO-2,6-DIHYDROXYPYRIMIDINE, THE SECOND PRODUCT OF THE RIBOFLAVIN SYNTHETASE REACTION. J Biol Chem. 1964 Oct;239:3493-7. [PubMed:14245407 ]

Enzymes

Enzyme Details
1. 14 kDa phosphohistidine phosphatase
General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available